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Practical Go-to-Market guidance specifically for B2B software and service companies between $5MM-$50MM in revenue.
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#46: Selling From The Outside In
Imagine a sales process that's as intuitive and reliable as buying from Amazon—our latest episode of the GTM Pro Podcast promises to show you how. We explore the groundbreaking role of digital sales rooms in complex sales processes and why understanding the buyer's procurement journey is crucial for decision-making confidence. Plus, learn from industry leaders and a compelling CEO conversation about the power of asking the right questions to decode customer priorities.
Welcome to the GTM Pro Podcast, your essential audio resource for mastering go-to-market discussions in the boardroom. Here we share insights for revenue leaders at B2B software and services companies, especially those with less than $50 million in revenue. Why? Because the challenges faced by companies of this size are unique. They are too big to be small and too small to be big. This dynamic pushes revenue leaders into executive leadership without a lot of help or support. We are here to provide that support. Your journey to boardroom excellence starts now.
Gary:Now, all right, welcome back to GTM Pro. We were just riffing on this, so we're excited to dive in. We are going to cover selling from the outside in and obviously that's going to align with the buyer led growth mindset. But here's kind of what we've been. Well, we've seen this for a while, but really you know kind of all coming together and it really revealed itself as we started to dig in and have some really direct experience with what's commonly referred to as digital sales rooms buyer packages, evaluation guides, a bunch of different ways to think about it, and I would say the genesis for most of these is the recognition that in complicated sales processes we have to send over a series of sequences of information, especially if we start to get into proofs of concepts and pilots and things like that, it gets really difficult to keep all that organized. So for a long time we'd send over via email PDFs and links and things like that and it would satiate the need in the moment. But then it was hard to keep that all together, especially when we're having to share different information with different stakeholders. We had a lot of sales enablement tools, if you will. That started with just really more from a marketing perspective helping teams organize content, marketing teams organize content for their sellers. Then we moved more into this.
Gary:You know the current incarnation of quote digital sales rooms, which is now incorporating comments and feedback and being able to track usage and things like that. But now we're evolving further because of what we're seeing with call recordings and AI is that we now really have an opportunity to flip the process where what we are doing is enabling the buyer to buy. And it's pretty profound if you think about the implications, because now, as we are doing our discovery discovery done well, as we've covered in the last two or three episodes is really getting inside the mind of the buyer and understanding the dynamics of the organization, what they're trying to do. It's really walking a mile in their shoes and then being able to condense that into a document that helps them articulate the problem, what they're trying to accomplish, clarify those things. That information can go back into Salesforce for notes. It's made available to the customer through this digital sales room, but now we have calls that are recorded and we have AI tools that can begin to do some of that note-taking for us and also begin to recommend things content that we may want to provide or talk tracks that we may want to think about.
Gary:And it doesn't stop there, because the whole idea especially when you're selling complicated products and you have multiple stages and multiple people involved there can be sections of this quote digital sales room that are relevant for technology, for the tech team, for the security team, for the legal team, but it's all in one place around this deal.
Gary:And then that becomes the perfect handoff component as we start to think about getting to the moment of value, the activation period. We're not having to start all over again from that. So you can see how this digital sales room, taken to its end use, is really the vehicle that allows us to build our sales process around how the buyer buys, down to the point where what we would advise is even beginning to change the names and types and number of stages that you have in your pipeline to map against your traditional buyer experience based on where they are, which gets difficult because every buyer is going to be a little bit different, but it creates a new set of challenges. But it's also much more reliable in terms of understanding where a buyer is in their process. So that's all the ingredients that come together in this concept of outside-in.
Andy:I'm going to go a little abstract which is so if you have an e-commerce platform as a typical sales process, a buyer led approach would look a lot more like Amazon, because they've already figured out so many things that a buyer needs before they feel good about making a purchase. Cause you're most often I, I think certainly with a lot of like kind of you know, random shopping that I do. I've never bought one of these products before. I'm just like I need this thing and, lo and behold, you can find about five versions of it on Amazon. Right, and they have put those things in such a way and encapsulated the information and the reviews and so on in a way that you can quickly get to a point of decision.
Andy:Confidence, right, and in typical sales processes, we're doing self-serving things.
Andy:We're trying to figure out how big a company is, we're trying to figure out, like, how many seats we might be able to sell them, and so on.
Andy:Right, as opposed to putting ourselves in the position of how can I enable that buyer to see their life in the future? And half the time, or more than half the time, we know more about a lot of things that they might be going through there and, for some reason or another, we don't share that we don't share the buying experience in the deal room. As a perfect example, right, we know what their procurement process probably looks like, and if this champion is a younger, newer employee they haven't been through it a bunch of times we can help them out so much and, for whatever reason, we just don't see that happen a whole lot. But that really is, I mean, funny. You say that like buyer. You know we talk about buyer led and we were just laughing about it earlier that I keep having epiphanies about this, like why can't we just sell more like we were in the buyer's shoes and you're like well, that's fire.
Andy:It really does keep hitting me that it's such a profound thing. And now to your point. There's more and more tools available to really make that happen. And then the counterpoint to that is there's more options for the buyer. There's more complexity. It's harder to learn about everything out there. So we have to we really have to help them with that.
Gary:Yeah, well, that's actually your great point is that all of this is actually in service to getting to confidence. So before I jump into that, I know I've shared this before this story before the analogy. I just can't remember if we did it on the GTM Pro podcast or not. So if you've heard this before, humor me, but it reminds me of.
Gary:I got to know a gentleman through a business group here in Charlotte and he happened to own a auto service shop, right, kind of a dive little place over on this industrial street in Charlotte, but super nice guy and was really, you know, it was really plugged in and, and so, you know, having four kids, I had aging vehicles that required service, and so, um, I took a minivan over to him and it was having all kinds of problems, probably 13 years old, um, and, and he, you know, they go away, they do their diagnostic and he comes back in and says, all right, well, we've got three options that we can do here, and he's. Then he asked a few questions. So, you know, how long are you going to own this thing? I'm like, well, you know, I'd love to get another two or three years out of it if I can. Um, well, how do you drive it? You know is, are you just driving it back and forth or you, you know? And he was asking some questions like, okay, well then this was the kicker, if I were you right, if it was me, and it was my vehicle.
Gary:And so he just took himself out of the sales person's role and walked alongside of me, put his arm around me as the buyer and said I have domain expertise that you do not. But I'm going to put myself in your shoes and I'm going to tell you what I would do if I were in your shoes, based on what I know. And he gave me three options and he's like I would pick option B and here's why I would pick option B. And I, you know, at that point I was supremely confident. I'm like, yes, let's do that. He was anticipating what I was thinking, what would be important to me, where I was, what made sense. And it wasn't the cheapest option, but it wasn't the most expensive option either. He was genuinely trying to get me to that and because he provided three options and didn't just say here's what I would do, I had even more confidence because now I was understanding how we compare and contrast and make trade-offs.
Andy:Yeah, the thought process and the inputs that went into why that made sense.
Gary:And, by the way, it wasn't an inexpensive fix. It was just not as expensive as it could have been. But I was not happy to make that investment, but I was confident, like I know, all right, I know I'm doing the right thing. I'm spending. This is money spent wisely. This is going to get me to wrapped up in just how can we convince them of the value, that the ROI, the return, that this investment makes sense and we're all triggered towards signing the contract when we say over and over again that the contract is just one stop on a journey towards what the buyer really wants, which is to the first moment of impact?
Gary:And if you back up and you look at it, for what are all the things that they're considering that are blocking or creating challenges for them to make a decision? It's not just signing the contract, it's a decision. I'm like, well, how much experience do they have around this? What are the other competing priorities? What other departments are required? I have personally been in buying situations where we were about to make an investment in a tool that made a world of sense for the business, for the department, for our goals, for everything, but it required two different product groups to change their roadmaps to make the implementation necessary to get to that moment of value. And they didn't want to do it because it wasn't their priority. Guess what Deal died?
Gary:Yeah, it died Part of the equation, despite the fact that we had the best ROI, we had all the things, but it died.
Andy:It was part of the equation.
Gary:And it was one of those things. To your point, andy, as the buyer, I was the champion on the deal and the economic buyer and I didn't foresee that was going to be. I knew it was going to be a challenge, but I didn't foresee that. But you know what? We hit a quarter priorities changed. We had a big customer come in, they hijacked the roadmap on the product and that was it, like there was nothing we could do about it Part of the product.
Andy:by the way, we say that too right, like if you, if your product requires um the customer to do something even remotely significant on their end, it's part of the product.
Gary:Yeah.
Andy:That was part of the product and, honestly, that sales team possibly could have helped you foresee that.
Gary:Well, they did not do a very good job of exploring it, because I knew what had to be done, but I don't know that they realized, you know, in our ecosystem what was what was required by that and where the tech was documentation and all that it was.
Gary:Everything was focused around roi, the value, what you're going to be able to do, like the gap and I even saw this thing recently with gap selling which is, you know, here's the current state, here's where you are, what the gap I'm like, but that tends to hone so much in on this I need to convince you that there's this value.
Gary:More often than not, are the things that kill deals right and not thinking through that process, and so that is.
Gary:It's interesting how we've been talking about the tools that we can use and training and all of these things, but I think probably the biggest challenge that we as sellers have is that we have done a horrible job of equipping our organization with a deep understanding of what it is like in our buyer's shoes.
Gary:We bring people in and we train them on process and we train them on the category and what our product does and a little bit on workflows and things like that, but they really don't have an understanding of what it's like to be in that role in a department, in a company that looks like this, with these goals, all the intricate stakeholders, and it's only getting harder right. The leaner we get, the more interconnected all of these departments become, the more stakeholders and shadow buyers we have. It really is getting difficult, and so we can train a sales rep all day long on how to ask questions to get the value. They can ask the questions and they're going to get answers, but if they don't understand the point of view from which the answer comes, they'll never know enough to answer or ask the second, third and fourth level question that actually get to the root of the matter.
Andy:Your car repair story totally reminded me of April Buys a Toilet which I've already talked about that sounds like a kid's book April Buys a Toilet.
Gary:April Buys a Toilet.
Andy:April Dunford sales pitch, check it out. Yeah, sales pitch was formative for me on a number of fronts. Where I think you're going there, gary too, is the pitch right. So I think companies take a stab at the pitch and if we use the April Buys a Toilet example, it might be this gold-plated, really cool toilet. Really cool because we hear that a lot around features is going to increase the value of your home because in this bathroom remodeling which she was doing, it's going to, like, accentuate the entire bathroom and it's going to increase the value of your home.
Andy:That's a sales pitch completely out of touch with where she was at from a buyer's perspective and where probably a lot of buyers were at. Where that happens in companies all the time, they take a stab at the value prop and the sales pitch and then they leave it up to the sales team to say, ok, does this work? Sometimes they don't even ask for feedback on that. It just goes out into the wild. The sales team fends for themselves and then ultimately, they come up with their own sales pitch, maybe each one individually, and they're all doing a different thing and there's no feedback loop on that.
Andy:Getting to in the April buys a toilet example, which is the salesperson who got down to brass tacks with her and said how big a space do you have for this? Do you care if it's fancy and glamorous and gold-plated? Do you want to use it every day? And those being the facets, we're down to this set right, and so you take those two extremes right when we're like letting sales fend for themselves, we're creating a sales pitch in a vacuum, and then things happen and it evolves and it turns into this other thing versus let's just start with good discovery, which we know is based on facts that our customers care about because we've asked them yeah, and so we just had a conversation with the CEO.
Gary:We were talking through. What we've observed from sales experience and he shared, as we've heard and seen from a lot of folks, is that the sales reps and this was a complicated sales process, but the sales reps that had a quote, a playbook, a process and they just ran the plays right. Reps that had a quote, a playbook, a process and they just ran the plays right. It's a you know, plan the day and run the plan. Um, we're by far the most successful right, and so that's how we end up with a lot of structure and rigor around the process. The challenge, back to your point, Andy is in some ways, running the process will have you asking the correct questions because, well, I guess that's outside of tech, where almost the traditional field sales role, where it's kind of trial by fire right in an environment and maybe they get a little bit of sales training on process and how to ask open door questions and how to be a closer and things like that. But for the most part, every individual sales person has their own little playbook. We see that pretty consistently and what we end up with then is, well, we need to find more Andys Like let's go hire another Andy because Andy does great, he's got all these relationships and finds a way to close deals and so we need another Andy. Problem is you go through two, three, four people and you don't find an Andy. And they're there for six, nine months and then they leave, and so that time that you lose is actually more valuable than the money that you spend, because you've lost the benefit of compounding versus. And you see this more in, I would say, newer technology companies with more of an SMB motion, where you have some younger sellers and it's really important that you have a pretty rigorous structure that you're bringing people into, especially if you're scaling, because you're adding new people all the time and you got to bring them into some structure. But in both cases, if you over-index on the process, then you're limiting your potential because they're just going to run the process without really understanding why they're asking the questions and what they're looking for.
Gary:And that's where it amazes me how few organizations just constantly work to extract for everybody not just sales, for marketing, for customer success, for anybody that's, frankly anybody in the organization Like here is what it is like to be one of our buyers, not buyers from a here's the process of buying software. But what do they do every day? What are they dealing with? What are the challenges? Because then, and only then, can you intelligently empathize with.
Gary:Okay, I know where you are Now I can put. The advantage that I have, even if I'm younger in my career, is that I have seen way more reps, way more not sales reps, but I've seen more data points, more situations, more than you will ever see, because this is my business. I sell prop tech, I sell property tech, and I see a lot of different property, a lot of different situations, and I can provide guidance on what I see with some technical specificity. So that, to me, is where, if you really want to move the needle, yes, process is good, having a structured process, but and continually informing that and building it around a thorough understanding of the buyer, especially if your process is built around the way the buyer buys is game changing.
Andy:I just simply like the notion of asking binary questions to narrow it down for starters, Like what matters to you this or this? Okay, that, really. That narrows it down quite a bit. Like we don't see that a lot, we see. What do you think of this cool feature?
Gary:Right.
Andy:And it leaves so many unanswered open questions for the buyer to be like how would I use this? And it happens. And of course there's successful deals happening all the time where the buyer and I say successful deal, getting to closed one. And, to your point, that's not the full battle, right. So we got them there, maybe because the feature looked really cool and they could scenario build in their head to say I could see our team and myself using it for these purposes and that is better than what we do. And that happens all the time. But it's not, to your point, rigorous around a process of getting to what's best for the customer. It's saying I'm kind of just selling what I think might be enticing and appealing to you and it's up to you to figure out if that's the right thing for you.
Gary:Yeah.
Gary:It's pretty different, and one of the reasons that, using your toilet analogy how many times have we said the word toilet in this podcast? It's kind of funny Is that you mentioned like the series of binary questions that allow you to narrow it in. That is actually really hard to do if you think about the level of expertise required to be able to do that. And that is where I think most companies fail in terms of training their reps is that we train them on our product and a need to understand that. And that is where I think most companies fail in terms of training their reps is that we train them on our product and a need to understand that. But inevitably, and probably obviously unintentionally, what we do is we have our salespeople then over index on our product and throw it over the wall for the buyer to have to figure out what you know, what does that mean for implementation and what does this mean, and so they're almost ill-equipped to ask those binary questions because we've not given them the full breadth of you know, if you think about the example that you provide, like that rep not only is responsible for that line of product but obviously is a consumer of that as well and therefore understands the questions.
Gary:That is something that most almost every business person, every salesperson especially doesn't have. That luxury Like they've never used cybersecurity tools. They can sell them, they can sell them fine, but they've never actually been tools. They can sell them, they can sell them fine, but they've never actually been a CIO in an organization or even a DevOps person who's responsible for cybersecurity. So so what do we do? We'll? That's where we have cybersecurity experts inside the four walls of the organization. There are people who build product around it. There are probably our founders who started this thing based on personal pain. We have customers that are using it every day, like the information exists, it's there. We just don't go get it and we don't do it in a consistent enough manner, in a package manner that we're and I and I guess to you know that's the concept here and I guess the challenge for us all as we think about you know how do you take action on?
Gary:This is part of what we provided at GTM Pro is what we call a discovery playbook, and it starts with a rigorous definition of ideal customer profile, buyer roles and problem statements. And if you do that from the perspective of the other thing that I'm thinking we should actually add to this is also the buyer process, because if you layer all those things together, you'll begin to understand how hard it is to actually buy something in today's modern organization and what we need to do to help them buy. Areas where there's extreme cynicism or skepticism, lack of confidence, lack of information, lack of experience, the interconnected nature of which departments need to be involved in which order? How to build the business case, how to create this as the priority over all the other priorities in the firm. How to build the business case, how to create this as the priority over all the other priorities in the firm. Right, spend more time on how our buyer buys and then focus on how we sell, and so often we're focused on the other way, and so it is truly a time where we're seeing this evolution of.
Gary:We need to build our process around the way the buyer buys Because, first of all, there are tools out there that are making it more transparent, that are allowing us to share information back and forth, that are giving us external signals as well as internal signals to be able to act on, giving us external signals as well as internal signals to be able to act on. So the sellers, the organizations that lean into this are really going to benefit from that, and it's like you said at the very beginning, andy it is the most powerful feedback loop you can have. It will tell you everything about where your buyers are thinking. Are you on to the right ideal customer profile? And it goes directly then to activation and retention. Like we now thoroughly understand the roadblocks that you may have. We may have been successful in selling it to you, but there's a lot of boulders that need to be moved for you to get to the appropriate moment of value that causes you to retain. That should not be a secret when we get started.
Andy:Yeah, and I think it's like you know, getting on board with this is, if you're feeling the no decision scenario creeping up more and more with customers, we wouldn't be surprised because people have been burned. There's there's so many choices it's easy to to gravitate toward. This is the devil. I know, um, you know it's not, I know it's not perfect, but I'm I'm at least comfortable with it. Right, and getting people to comfort, to your your car repair he got you to comfort. Like he got you to comfort. It wasn't your favorite thing to spend that much on an aging vehicle, but he got you to comfort. And that is what, like I think that's hugely lacking is. I feel comfortable here. I feel pressure, I feel FOMO, fear, uncertainty and doubt when I speak to a salesperson, but I don't feel comfort very often.
Gary:Indeed.
Andy:Okay.
Gary:So, if you are finding more and more deals lost to no decision and or really struggling with how you can create a repeatable, scalable framework to do this, we'd love for you to go check out gtmproco. We recently launched a service that gets you to a good foundation for a discovery playbook and then how to execute and run that playbook discovery playbook and then how to execute and run that playbook Um, it's very tight, very short, very high value. You can get to. You can get to action quickly. So, um, you know, check it out. We'd love your feedback in. Uh, let us know. But until then, next week we'll be back with more GTM pro. Until then, go be a pro. See, ya, Thank you for tuning in to GTM Pro, where you become the pro. We're here to foster your growth as a revenue leader, offering the insights you need to thrive. For further guidance, visit gtmproco and continue your path to becoming board ready with us. Share this journey, subscribe, engage and elevate your go-to-market skills. Until next time, go be a pro.